Product Name

  • Name

    15-Crown-5

  • EINECS 251-379-6
  • CAS No. 33100-27-5
  • Article Data27
  • CAS DataBase
  • Density 0.995 g/cm3
  • Solubility MISCIBLE
  • Melting Point -20oC
  • Formula C10H20O5
  • Boiling Point 350.9 °C at 760 mmHg
  • Molecular Weight 220.266
  • Flash Point 139.1 °C
  • Transport Information
  • Appearance colourless liquid
  • Safety 26-39-36
  • Risk Codes 22-36/38-36-20/22-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 33100-27-5 (15-Crown-5)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms 5-19-12-00252 (Beilstein Handbook Reference);1,4,10,13-Pentaoxacyclopentadecane;15-crown-5 ether;15-Crown-5(1,4,7,10,13-Pentaoxacyclopentadecane);
  • PSA 46.15000
  • LogP 0.08300

Synthetic route

1,4,7,10,13-pentaoxacyclopentadecane-2,6-dione
63689-58-7

1,4,7,10,13-pentaoxacyclopentadecane-2,6-dione

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h;79%
Pentaethylene glycol
4792-15-8

Pentaethylene glycol

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 80℃;75%
With sodium hydroxide; p-toluenesulfonyl chloride In 1,2-dimethoxyethane at 0℃; Product distribution; var. solvents, reagents, and temp.; other oligoethylene glycols;36 % Chromat.
Tetraethylene glycol
112-60-7

Tetraethylene glycol

ethylene glycol
107-21-1

ethylene glycol

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
With sodium carbonate; dicyclohexyl-carbodiimide In 1,4-dioxane at 70 - 75℃; for 6h; Concentration; Reagent/catalyst; Temperature; Solvent;70.2%
3-oxa-1,5-dichloropentane
111-44-4

3-oxa-1,5-dichloropentane

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
With sodium methylate In 1,4-dioxane for 24h; Heating; metal hydroxides, different bases as 'template' agents;66%
With sodium methylate In 1,4-dioxane for 24h; Heating;66%
1,4,7,10,13-Pentaoxacyclopentadecane-2,3-dithione
86309-76-4

1,4,7,10,13-Pentaoxacyclopentadecane-2,3-dithione

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
With nickel In diethyl ether; dichloromethane at 0℃; for 1h;52%
Pentaethylene glycol
4792-15-8

Pentaethylene glycol

A

15-crown-5
33100-27-5

15-crown-5

B

<60>crown-20
71092-63-2

<60>crown-20

C

<30>crown-10
52985-64-5

<30>crown-10

D

45-Crown-15
109635-67-8

45-Crown-15

Conditions
ConditionsYield
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃;A 46%
B 0.7%
C 12%
D 3.4%
Pentaethylene glycol
4792-15-8

Pentaethylene glycol

A

15-crown-5
33100-27-5

15-crown-5

B

<30>crown-10
52985-64-5

<30>crown-10

C

45-Crown-15
109635-67-8

45-Crown-15

Conditions
ConditionsYield
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃;A 46%
B 12%
C 3.4%
1,2-bis(2-chloroethoxy)ethane
112-26-5

1,2-bis(2-chloroethoxy)ethane

diethylene glycol
111-46-6

diethylene glycol

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
With potassium hydroxide for 0.133333h; microwave irradiation;40%
diethylene glycol ditosylate
7460-82-4

diethylene glycol ditosylate

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
With aluminum oxide; potassium fluoride In acetonitrile for 24h; Ambient temperature;25%
18-crown-6 ether
17455-13-9

18-crown-6 ether

C14H14Mg*C10H20O5

C14H14Mg*C10H20O5

A

15-crown-5
33100-27-5

15-crown-5

B

C14H14Mg*C12H24O6

C14H14Mg*C12H24O6

Conditions
ConditionsYield
In benzene at 25℃; Equilibrium constant;
complex of 15-crown-5 with K+
61060-13-7

complex of 15-crown-5 with K+

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
In methanol at 25℃; Equilibrium constant;
In acetone at 25℃; Equilibrium constant; complexation of alkali metal cations (Li+, Na+, K+, Rb+, Cs+) with crown ethers, diaza crown ethers and cryptands in acetone, stability constants of complexes formed; influence of ion-pair formation on stability constants;
complex of 15-crown-5 with Na+
59890-71-0

complex of 15-crown-5 with Na+

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
In methanol at 25℃; Equilibrium constant;
complex of 15-crown-5 with Na+
59890-71-0

complex of 15-crown-5 with Na+

A

15-crown-5
33100-27-5

15-crown-5

B

sodium cation
17341-25-2

sodium cation

Conditions
ConditionsYield
In methanol; water at 25℃; Equilibrium constant; var. MeOH/H2O ratio;
C10H20O5*C6H2N3O7(1-)*K(1+)

C10H20O5*C6H2N3O7(1-)*K(1+)

A

15-crown-5
33100-27-5

15-crown-5

B

potassium picrate
573-83-1

potassium picrate

Conditions
ConditionsYield
In dichloromethane; water at 25℃; for 0.666667h; Equilibrium constant;
C10H20O5*C6H2N3O7(1-)*Cs(1+)

C10H20O5*C6H2N3O7(1-)*Cs(1+)

A

15-crown-5
33100-27-5

15-crown-5

B

cesium picrate
3638-61-7

cesium picrate

Conditions
ConditionsYield
In dichloromethane; water at 25℃; for 0.666667h; Equilibrium constant;
C10H20O5*C6H2N3O7(1-)*Na(1+)

C10H20O5*C6H2N3O7(1-)*Na(1+)

A

15-crown-5
33100-27-5

15-crown-5

B

sodium picrate
3324-58-1

sodium picrate

Conditions
ConditionsYield
In dichloromethane; water at 25℃; for 0.666667h; Equilibrium constant;
C10H20O5*C6H2N3O7(1-)*Rb(1+)

C10H20O5*C6H2N3O7(1-)*Rb(1+)

A

15-crown-5
33100-27-5

15-crown-5

B

rubidium picrate
23296-29-9

rubidium picrate

Conditions
ConditionsYield
In dichloromethane; water at 25℃; for 0.666667h; Equilibrium constant;
C10H20O5*C7H7N2(1+)*BF4(1-)

C10H20O5*C7H7N2(1+)*BF4(1-)

A

15-crown-5
33100-27-5

15-crown-5

B

2-methylchlorobenzene
95-49-8

2-methylchlorobenzene

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; Rate constant; Kinetics; Thermodynamic data; var. crown ethers, ΔH(excit.), ΔS(excit.);
C10H20O5*C8H9N2(1+)*BF4(1-)

C10H20O5*C8H9N2(1+)*BF4(1-)

A

15-crown-5
33100-27-5

15-crown-5

B

1-chloro-2-ethylbenzene
89-96-3

1-chloro-2-ethylbenzene

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; Rate constant; Kinetics; Thermodynamic data; var. crown ethers, ΔH(excit.), ΔS(excit.);
o-acetylbenzenediazonium tetrafluoroborate

o-acetylbenzenediazonium tetrafluoroborate

A

15-crown-5
33100-27-5

15-crown-5

B

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; Rate constant; Kinetics; Thermodynamic data; var. crown ethers, ΔH(excit.), ΔS(excit.);
C10H20O5*C3H9N*H(1+)

C10H20O5*C3H9N*H(1+)

A

15-crown-5
33100-27-5

15-crown-5

B

trimethylammonium
145384-53-8

trimethylammonium

Conditions
ConditionsYield
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D;
C10H20O5*C6H13N*H(1+)

C10H20O5*C6H13N*H(1+)

A

cyclohexyl-ammonium cation
29384-28-9

cyclohexyl-ammonium cation

B

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D;
C10H20O5*C5H5N*H(1+)

C10H20O5*C5H5N*H(1+)

A

pyridin-1-ium
16969-45-2

pyridin-1-ium

B

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D;
triethylene glycol di-(p-toluenesulfonate)
19249-03-7

triethylene glycol di-(p-toluenesulfonate)

diethylene glycol
111-46-6

diethylene glycol

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
With aluminum oxide; potassium fluoride In acetonitrile for 24h; Ambient temperature;33 % Chromat.
C10H20O5*ClO4(1-)*Li(1+)

C10H20O5*ClO4(1-)*Li(1+)

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
In acetone Equilibrium constant; various solvents (MeNO2, MeCN, propylene carbonate, MeOH, pyridine), complex formation between crown ethers and lithim ion, effect of solvent of the stability of complexes, 7Li NMR study;
In acetone Equilibrium constant; various solvents (MeNO2, MeCN, MeOh H2O etc.), complex formation between crown ethers and lithim ion, effect of solvent of the stability of complexes;
1,4,7,10,13-Pentaoxa-cyclopentadecane; compound with GENERIC INORGANIC NEUTRAL COMPONENT

1,4,7,10,13-Pentaoxa-cyclopentadecane; compound with GENERIC INORGANIC NEUTRAL COMPONENT

15-crown-5
33100-27-5

15-crown-5

Conditions
ConditionsYield
With Iodine monochloride In benzene at 24.9℃; Equilibrium constant;
complex of 15-crown-5 with K+
61060-13-7

complex of 15-crown-5 with K+

cryptand 211
31250-06-3

cryptand 211

A

15-crown-5
33100-27-5

15-crown-5

B

C14H28N2O4*K(1+)

C14H28N2O4*K(1+)

Conditions
ConditionsYield
In gas at 76.9℃; Equilibrium constant; Thermodynamic data; ΔG0;
complex of 15-crown-5 with Na+
59890-71-0

complex of 15-crown-5 with Na+

cryptand 211
31250-06-3

cryptand 211

A

15-crown-5
33100-27-5

15-crown-5

B

C14H28N2O4*Na(1+)

C14H28N2O4*Na(1+)

Conditions
ConditionsYield
In gas at 76.9℃; Equilibrium constant; Thermodynamic data; ΔG0;
C10H20O5*Li(1+)
74060-72-3

C10H20O5*Li(1+)

cryptand 211
31250-06-3

cryptand 211

A

15-crown-5
33100-27-5

15-crown-5

B

C14H28N2O4*Li(1+)

C14H28N2O4*Li(1+)

Conditions
ConditionsYield
In gas at 76.9℃; Equilibrium constant; Thermodynamic data; ΔG0;
15-crown-5
33100-27-5

15-crown-5

[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]
851576-85-7

[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]

sodium hexamethyldisilazane
1070-89-9

sodium hexamethyldisilazane

[(OC)5WP(CH(SiMe3)2)CNNa(15-crown-5)]
947333-62-2

[(OC)5WP(CH(SiMe3)2)CNNa(15-crown-5)]

Conditions
ConditionsYield
In tetrahydrofuran under Ar; cooled (-80°C) soln. of NaN(SiMe3)2 in THF added dropwise to stirred soln. of W complex in THF and 15-crown-5; warmed slowly toroom temp. for 3.5 h; solvent removed under vac.; washed with Et2O and n-pentane; dried under reduced pressure; elem. anal.;100%
15-crown-5
33100-27-5

15-crown-5

Br(1-)*C10H20NaO5

Br(1-)*C10H20NaO5

Conditions
ConditionsYield
With sodium bromide In water at 20℃; for 12h;100%
15-crown-5
33100-27-5

15-crown-5

C10H20NaO5*HO(1-)

C10H20NaO5*HO(1-)

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 12h;100%
15-crown-5
33100-27-5

15-crown-5

C10H20NaO5*IO3(1-)

C10H20NaO5*IO3(1-)

Conditions
ConditionsYield
With sodium iodate In water at 20℃; for 12h;100%
15-crown-5
33100-27-5

15-crown-5

sodium acetate
127-09-3

sodium acetate

C2H3O2(1-)*C10H20NaO5

C2H3O2(1-)*C10H20NaO5

Conditions
ConditionsYield
In water at 20℃; for 12h;100%
15-crown-5
33100-27-5

15-crown-5

sodium oxalate
62-76-0

sodium oxalate

C2O4(2-)*2C10H20NaO5

C2O4(2-)*2C10H20NaO5

Conditions
ConditionsYield
In water at 20℃; for 12h;100%
15-crown-5
33100-27-5

15-crown-5

potassium hydrogen phthalate
877-24-7

potassium hydrogen phthalate

C8H5O4(1-)*C12H24KO6

C8H5O4(1-)*C12H24KO6

Conditions
ConditionsYield
In water at 20℃; for 12h;100%
15-crown-5
33100-27-5

15-crown-5

sodium chloride
7647-14-5

sodium chloride

zinc(II) chloride
7646-85-7

zinc(II) chloride

C10H20NaO5(1+)*Cl3Zn(1-)

C10H20NaO5(1+)*Cl3Zn(1-)

Conditions
ConditionsYield
Stage #1: 15-crown-5; sodium chloride In water at 20℃; for 12h;
Stage #2: zinc(II) chloride In ethanol for 12h; Reflux;
100%
15-crown-5
33100-27-5

15-crown-5

iron(III) chloride hexahydrate

iron(III) chloride hexahydrate

sodium chloride
7647-14-5

sodium chloride

Cl4Fe(1-)*C10H20NaO5(1+)

Cl4Fe(1-)*C10H20NaO5(1+)

Conditions
ConditionsYield
Stage #1: 15-crown-5; sodium chloride In water at 20℃; for 12h;
Stage #2: iron(III) chloride hexahydrate In ethanol for 12h; Reflux;
100%
hydrogenchloride
7647-01-0

hydrogenchloride

15-crown-5
33100-27-5

15-crown-5

uranyl acetate dihydrate

uranyl acetate dihydrate

sodium acetate
127-09-3

sodium acetate

2Na(1+)*2(CH2)10O5*UO2Cl4(2-)=[Na(CH2)10O5]2UO2Cl4

2Na(1+)*2(CH2)10O5*UO2Cl4(2-)=[Na(CH2)10O5]2UO2Cl4

Conditions
ConditionsYield
In water UO2OAc2*2H2O, NaCH3COO, ligand and HCl were combined in water with stirring, evapd. slowly at room temp. for 1 wks; isolated; elem. anal.;99.9%
15-crown-5
33100-27-5

15-crown-5

[NaU(bis(trimethylsilyl)amide)(CH2SiMe2N(SiMe3))2]
1242245-34-6

[NaU(bis(trimethylsilyl)amide)(CH2SiMe2N(SiMe3))2]

[Na(15-crown-5)][U(bis(trimethylsilyl)amide)(CH2SiMe2N(SiMe3))2]

[Na(15-crown-5)][U(bis(trimethylsilyl)amide)(CH2SiMe2N(SiMe3))2]

Conditions
ConditionsYield
In pentane under Ar; a NMR tube was charged with U-contg. compd. (0.027 mmol) in pentane, and 15-crown-5 (0.032 mmol) was added; the suspn. was heated for 3 d at 60°C; elem. anal.;99%
15-crown-5
33100-27-5

15-crown-5

1,1,1-trimethyl-2,2,2-triphenyldisilane
1450-18-6

1,1,1-trimethyl-2,2,2-triphenyldisilane

[Na(15-crown-5)SiPh3]·(thf )0.5

[Na(15-crown-5)SiPh3]·(thf )0.5

Conditions
ConditionsYield
With sodium t-butanolate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;99%
sodium amalgam

sodium amalgam

15-crown-5
33100-27-5

15-crown-5

C60H51B3N12(1-)

C60H51B3N12(1-)

C60H51B3N12(1-)*C10H20NaO5(1+)

C60H51B3N12(1-)*C10H20NaO5(1+)

Conditions
ConditionsYield
In tetrahydrofuran; hexane99%
15-crown-5
33100-27-5

15-crown-5

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

sodium fluoride

sodium fluoride

{Na-15-crown-5}2-cis-{ZrF2Cl4}

{Na-15-crown-5}2-cis-{ZrF2Cl4}

Conditions
ConditionsYield
In acetonitrile soln. of ZrCl4 and 15-crown-5 prepared under cooling; addn. of NaF; stirred for 12 h at 25°C; filtration; solvent removed until beginning of crystn.; cooled down to 5°C; crystn.; filtration; washed (cold acetonitrile); dried under vac.; elem. anal.; IR;98.3%
15-crown-5
33100-27-5

15-crown-5

niobium pentachloride

niobium pentachloride

(NbCl4)2(15-crown-5)

(NbCl4)2(15-crown-5)

Conditions
ConditionsYield
In tetrachloromethane Ar-atmosphere; room temp.; elem. anal.;98%
15-crown-5
33100-27-5

15-crown-5

Na[U(N(SiMe3)2)(OC(=CH2)SiMe2NSiMe3)2(N3)]
1331740-29-4

Na[U(N(SiMe3)2)(OC(=CH2)SiMe2NSiMe3)2(N3)]

pentane
109-66-0

pentane

Na(C10H20O5)[U(N3)(NSi2C6H18)(COCH2Si(CH3)2N(Si(CH3)3))2]*0.5C5H12

Na(C10H20O5)[U(N3)(NSi2C6H18)(COCH2Si(CH3)2N(Si(CH3)3))2]*0.5C5H12

Conditions
ConditionsYield
In pentane Ar; U compd. and ligand (1:1 molar ratio), stirred for 12 at 20°C; filtered, evapd., elem. anal.;98%
iron(II) bis(trimethylsilyl)amide
14760-22-6

iron(II) bis(trimethylsilyl)amide

15-crown-5
33100-27-5

15-crown-5

sodium hexamethyldisilazane
1070-89-9

sodium hexamethyldisilazane

[Na(15-crown-5)2]+[Fe(N{SiMe3}2)3]−

[Na(15-crown-5)2]+[Fe(N{SiMe3}2)3]−

Conditions
ConditionsYield
Stage #1: iron(II) bis(trimethylsilyl)amide; sodium hexamethyldisilazane In toluene for 1h; Reflux; Inert atmosphere; Glovebox; Schlenk technique;
Stage #2: 15-crown-5 In toluene for 1h; Reflux; Inert atmosphere; Glovebox; Schlenk technique;
97.74%
15-crown-5
33100-27-5

15-crown-5

dihydroxy-anthraquinone-C60

dihydroxy-anthraquinone-C60

bis(sodium-15-crown-5)dioxoanthraquinone-C60

bis(sodium-15-crown-5)dioxoanthraquinone-C60

Conditions
ConditionsYield
With sodium t-butanolate In tetrahydrofuran; toluene Ambient temperature;97%
ammonium dichromate(VI)

ammonium dichromate(VI)

15-crown-5
33100-27-5

15-crown-5

NH4CrO3Cl(15-crown-5)2

NH4CrO3Cl(15-crown-5)2

Conditions
ConditionsYield
With hydrogenchloride In water addn. of org. ligand to soln. of ammonium dichromate and concd. hydrochloric acid (stirring, 20°C); ppt. filtered off, washed (water) and dried at 40-50°C; elem. anal.;97%
15-crown-5
33100-27-5

15-crown-5

Ni(1,3-imidazolidinyl-N,N'-bis(benzene-2-thiolate)2) * DMF

Ni(1,3-imidazolidinyl-N,N'-bis(benzene-2-thiolate)2) * DMF

sodium thiophenolate
930-69-8

sodium thiophenolate

[Na(1,4,7,10,13-pentaoxacyclopentadecane)][Ni(SPh)(1,3-imidazolidinyl-N,N'-bis(benzene-2-thiolate))]

[Na(1,4,7,10,13-pentaoxacyclopentadecane)][Ni(SPh)(1,3-imidazolidinyl-N,N'-bis(benzene-2-thiolate))]

Conditions
ConditionsYield
In tetrahydrofuran N2-atmosphere; mixing Ni-complex with excess NaSPh, addn. of MeOH, stirring for 1 d, filtration, addn. of excess of crown; crystn. (-30°C, 3 d), collection (filtration), washing (THF, hexane), drying (vac., 2 h); elem. anal.;97%
2,6-dimesitylphenyl-trifluorosilane

2,6-dimesitylphenyl-trifluorosilane

15-crown-5
33100-27-5

15-crown-5

C10H20O5*C24H25F4Si(1-)*Na(1+)
1195787-45-1

C10H20O5*C24H25F4Si(1-)*Na(1+)

Conditions
ConditionsYield
With sodium fluoride In toluene for 648h; Inert atmosphere;97%
tin(II) trifluoromethanesulfonate

tin(II) trifluoromethanesulfonate

15-crown-5
33100-27-5

15-crown-5

[tin(II)([15]crown-5)2](trifluoromethanesulfonate)2

[tin(II)([15]crown-5)2](trifluoromethanesulfonate)2

Conditions
ConditionsYield
In tetrahydrofuran standard inert-atmosphere techniques; soln. of (15)crown-5 (0.972 mmol) added to soln. of Sn(OTf)2 (0.480 mmol), stiired for 2 h; solvent removed (in vac.), washed with pentane; elem. anal.;97%
15-crown-5
33100-27-5

15-crown-5

magnesium bis(tetrahydroborate) tris(tetrahydrofuran)

magnesium bis(tetrahydroborate) tris(tetrahydrofuran)

magnesium bis(tetrahydroborate) bis(15-crown-5)

magnesium bis(tetrahydroborate) bis(15-crown-5)

Conditions
ConditionsYield
In tetrahydrofuran96.1%
In tetrahydrofuran byproducts: THF; under N2 15-crown-5 was added dropwise to THF soln. of Mg-compd.; ppt. was centrifuged off, dried in vac., elem. anal.;96.1%
15-crown-5
33100-27-5

15-crown-5

MoF4(NCl)
113236-05-8

MoF4(NCl)

sodium fluoride

sodium fluoride

sodium-15-crown-5-pentafluoro-N-chloronitreno-molybdate(IV)

sodium-15-crown-5-pentafluoro-N-chloronitreno-molybdate(IV)

Conditions
ConditionsYield
In acetonitrile stirring (room temp., 2 h); crystn. on cooling (-18°C), sepn. (filtration off), washing (acetonitrile), drying (vac.); elem. anal.;96%
15-crown-5
33100-27-5

15-crown-5

niobium pentachloride

niobium pentachloride

(NbCl4)3(15-crown-5)

(NbCl4)3(15-crown-5)

Conditions
ConditionsYield
In tetrachloromethane Ar-atmosphere; molar ratio Nb2Cl10:crown=1:2, room temp.; elem. anal.;96%
2-(3-methoxymethoxyphenyl)butane-1,2-diol
131481-05-5

2-(3-methoxymethoxyphenyl)butane-1,2-diol

15-crown-5
33100-27-5

15-crown-5

methyl iodide
74-88-4

methyl iodide

2-methoxy-2-(3-methoxymethoxyphenyl)but-1-yl methyl ether
131480-48-3

2-methoxy-2-(3-methoxymethoxyphenyl)but-1-yl methyl ether

Conditions
ConditionsYield
In N-methyl-acetamide; mineral oil95%
15-crown-5
33100-27-5

15-crown-5

2Mo(6+)*2(N3S2)(3-)*6Cl(1-)={MoCl3(N3S2)}2

2Mo(6+)*2(N3S2)(3-)*6Cl(1-)={MoCl3(N3S2)}2

sodium fluoride

sodium fluoride

{Na-15-crown-5}{MoF2Cl2(N3S2)}

{Na-15-crown-5}{MoF2Cl2(N3S2)}

Conditions
ConditionsYield
In acetonitrile byproducts: NaCl; addn. of NaF to suspn. of Mo-complex, addn. of 15-crown-5 (dropwise), stirring (12 h), sepn. of ppt. (filtration); crystn. on cooling (-20°C), sepn. (filtration off), washing (acetonitrile), drying (vac.); elem. anal.;95%
15-crown-5
33100-27-5

15-crown-5

{ReCl3(NO)2}2

{ReCl3(NO)2}2

sodium fluoride

sodium fluoride

acetonitrile
75-05-8

acetonitrile

{Na(15-crown-5)}{ReFCl3(NO)(CH3CN)}

{Na(15-crown-5)}{ReFCl3(NO)(CH3CN)}

Conditions
ConditionsYield
In acetonitrile heating of 1.8mmol (ReCl3(NO)2)2 in 30ml acetonitrile (formation of sol. (ReCl3(NO)2(CH3CN)), addn. of 3.6mmol NaF amd 0.715ml 15 crown-5; 2h refluxing;; cooling down and concg. of soln.; single crystal;filtn., concgn. of filtrate (20ml); elem. anal.;;95%
aluminium trichloride
7446-70-0

aluminium trichloride

15-crown-5
33100-27-5

15-crown-5

{AlCl2((CH2CH2O)5)}(1+)*AlCl4(1-)={AlCl2((CH2CH2O)5)}{AlCl4}
111523-29-6

{AlCl2((CH2CH2O)5)}(1+)*AlCl4(1-)={AlCl2((CH2CH2O)5)}{AlCl4}

Conditions
ConditionsYield
In tetrahydrofuran all manipulations under dry N2; slowly dissolving AlCl3 in THF, adding 15-crown-5 with stirring, color change from light green to dark green, crystn. (after 30 min); sepg. crystals from the mother soln., drying (vac., 25°C); elem. anal.;95%
15-crown-5
33100-27-5

15-crown-5

scandium chloride * 3 acetonitrile

scandium chloride * 3 acetonitrile

(ScCl2(C10H20O5))(1+)*Cl(1-)=(ScCl2(C10H20O5))Cl
147631-11-6

(ScCl2(C10H20O5))(1+)*Cl(1-)=(ScCl2(C10H20O5))Cl

Conditions
ConditionsYield
In acetonitrile Sc-compd. was dissolved in MeCN (under dry inert gas), addn. of crown ether; sepn. of precipitate, washing with MeCN, vac. drying at 30°C, elem. anal.;95%

15-Crown-5 Chemical Properties


IUPAC Name: 3,6,9,12,15-Pentaoxacyclopentadecane
Molecular Formula: C10H20O5
Molecular Weight: 220.26 g/mol
Canonical SMILES: C1COCCOCCOCCOCCO1
InChI: InChI=1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
EINECS: 251-379-6
Classification Code: Drug / Therapeutic Agent; Skin / Eye Irritant
Product Categories: Crown Ethers; Functional Materials; Macrocycles for Host-Guest Chemistry
Stability: Stable. Incompatible with oxidizing agents, strong acids. Avoid exposure to water or moist air.
Water Solubility: Miscible
Sensitive: Hygroscopic
XLogP3: -0.5
H-Bond Acceptor: 5
Index of Refraction: 1.404
Molar Refractivity: 54.14 cm3
Molar Volume: 221.3 cm3
Polarizability: 21.46×10-24 cm3
Surface Tension: 31.2 dyne/cm
Density: 0.995 g/cm3
Flash Point: 139.1 °C
Enthalpy of Vaporization: 57.2 kJ/mol
Boiling Point: 350.9 °C at 760 mmHg
Water Solubility: 8.82E+04 mg/L at 25 °C
Henry's Law Constant: 2.22E-11 atm-m3/mole at 25 °C
Atmospheric OH Rate Constant: 7.01E-11 cm3/molecule-sec at 25 °C
Vapour Pressure of 15-Crown-5 (CAS NO.33100-27-5): 1.44E-03 mm Hg at 25 °C

15-Crown-5 Uses

 15-Crown-5 (CAS NO.33100-27-5) is used as phase transfer catalyst, metal complexing agent, selective removal and separation of cation.

15-Crown-5 Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 514mg/kg (514mg/kg) BEHAVIORAL: TREMOR
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
mouse LD50 oral 1020mg/kg (1020mg/kg) BEHAVIORAL: TREMOR Toxicology and Applied Pharmacology. Vol. 44, Pg. 263, 1978.
rabbit LD50 intraperitoneal 560mg/kg (560mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(2), Pg. 48, 1987.
rabbit LD50 skin 2520mg/kg (2520mg/kg) BEHAVIORAL: TREMOR
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rat LD50 intraperitoneal 530mg/kg (530mg/kg) BEHAVIORAL: TREMOR
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rat LD50 oral 1410mg/kg (1410mg/kg) BEHAVIORAL: TREMOR Drug and Chemical Toxicology. Vol. 1, Pg. 339, 1978.

15-Crown-5 Consensus Reports

Reported in EPA TSCA Inventory.

15-Crown-5 Safety Profile

Moderately toxic by ingestion, skin contact, and intraperitoneal routes. A skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:HarmfulXn, IrritantXi 
Risk Statements: 22-36/38-36-20/22-36/37/38-20/21/22 
R22: Harmful if swallowed. 
R36/38: Irritating to eyes and skin. 
R36: Irritating to eyes. 
R20/22: Harmful by inhalation and if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-39-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S39: Wear eye / face protection. 
S36: Wear suitable protective clothing.
RIDADR: 2810
WGK Germany: 3
Hazard Note: Irritant
HazardClass: 6.1(b)
PackingGroup of 15-Crown-5 (CAS NO.33100-27-5): III

15-Crown-5 Specification

 15-Crown-5 (CAS NO.33100-27-5), its Synonyms are 1,4,7,10,13-Pentaoxacyclopentadecane ; 15-Crown-5,1,4,7,10,13-Pentaoxa-cyclo-pentadecane ; Crownethers ; Ethyleneoxidecyclicpentamer ; Lead ionophore V . It is colourless liquid. It is a cyclic pentamer of ethylene oxide that has been shown to complex with various cations, including sodium (Na+) and potassium (K+), but selective binding to lead (Pb2+).

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